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The medicinal value of cow milk is well defined in ancient Indian literature of Ayurveda and Charak Samhita. Cow milk contains protein, fats and carbohydrates as its constituents. The ancient literature did not reveal which constituent of the milk carries its biological activities. With the advent of glycoscience it was postulated that the carbohydrates present in milk, in the form of oligosaccharide are responsible for its medicinal values. The oligosaccharide content of the milk depends on various factors i.e., breed of the animal, their food and geographical fauna around them. The cow milk carries brain stimulating, immunostimulant and bone developing properties. Keeping the above facts in mind we have collected the Kankerej cow milk from Rajasthan for the study of its oligosaccharide constituents. The milk was collected in bulk and was processed by modified method of Kobata and Ginsburg for obtaining its oligosaccharide contents. Further, it was chromatographed and purified by different chromatographic techniques for isolating the oligosaccharides in its purest derivatized form. Further, the structure elucidation of the purified oligosaccharide/oligoglycoside was performed by chemical transformation, chemical degradation, spectroscopic techniques such as 1H, 13C, HSQC, TOCSY, COSY, HMBC NMR spectroscopy and mass spectrometry. The structure of the isolated compound was deduced as pentaglycoside (Kankaroside). The structure of this novel oligosaccharide was established as under: β-Gal(1→4)-β-Gal(1-→4)-β-GalNAc(1→3)-β-Gal(l→4)-β-Glc-OCH3 [ABSTRACT FROM AUTHOR]

Position of glycosidic linkages in oligosaccharide was confirmed by alditol acetate. methylation/acid hydrolysis in traditional studies. Later. core units and structure reporter group theory along with comparison of chemical shifts of natural and acetylated oligosaccharides were used for confirming the position of glycosidic linkages. These methods were. however. inappropriate and imperfect in certain cases. In recent times. 2D heteronuclear multiple bond correlation (HMBC) NMR experiments are being used for this purpose. making it possible to fix the position of glycosidic linkages unequivocally. In this experiment the multiple bond correlation of anomeric carbon of next monosaccharide gives a cross peak with the methine proton of the previous monosaccharide in an oligosaccharide chain. It becomes more complicated when the oligosaccharide is comprised of long or branched chains. but due to some proximal and steric hindrances this correlation is often not observed restricting the process of sequencing in milk oligosaccharides. In these circumstances. an alternative experiment. Reverse HMBC is used and is explained for the first time. meaning thereby. we observe the cross peak between methine carbon of the monosaccharide under observation with the anomeric proton of the next monosaccharide. In the present paper. Reverse HMBC technique for structure elucidation of novel heptaglycoside named Arkaroside from Tharparkar cow milk has been used. [ABSTRACT FROM AUTHOR]

Milk is a biofluid. essential for growth and development of infants and is comprised of protein. fat and carbohydrates in the form of lactose and oligosaccharides. These oligosaccharides are responsible for any specific biological activity of the particular milk. Camel milk is called gold of dessert and has antitubercular. antiviral and antitumor properties. Camel milk also contains disease-fighting properties and have hypogylcemic activity. Keeping in mind, the usefulness of camel's milk and role of oligosaccharides present in it for treatment of various diseases. It was collected in bulk and processed by modified method of Kobata and Ginsberg method followed by Gel filtration. HPLC and silica column chromatography which led to isolation of a novel nonasaccharide. Ramedrose and its structure was elucidated with the help of ¹H, 13C NMR and 2D NMR i.e. HMBC. HSQC. COSY and TOCSY and Mass spectrometry which is as under (1→3)-α-D-Glc(1→3)-β-D-Glc(1→3)-β-D-Glc(1→3)-β-D-Gal(1→3)-β-D-GlcNAc(1→3)-β-D-GalNAc(1→4)-β-D-Glc ... [ABSTRACT FROM AUTHOR]

Yak (Bosgrunniens) is an inhabitant of the Himalayan regions like Sikkim, Bhutan and China. It belongs to the cow family and its milk is used for enema therapy in Tibet and also has immunostimulant properties. For isolation of its oligosaccharide contents, the milk was collected and processed by the modified method of Kobata and Ginsburg and was purified by combining gel filtration, HPLC and silica column chromatography resulting in the isolation of an undescribed branched chain octasaccharide 'Uniose'. The stereoscopic structure of Uniose was elucidated with the help of 1D (¹H, 13C), 2D NMR (HSQC, TOCSY, COSY and HMBC) and Mass spectrometry as under: ... Uniose [ABSTRACT FROM AUTHOR]

Goat milk oligosaccharides have anti-inflammatory properties and are involved in the repairing process after dextran sodium sulphate induced colitis. Keeping in mind the biological importance of goat milk oligosaccharides, goat milk was analyzed for its oligosaccharide content which led to the isolation of a novel heptasaccharide, Egarose, C48H81O36N3. The structure of the isolated oligosaccharide was elucidated by chemical transformation, chemical degradation, ¹H, 13C, 2D-NMR (HSQC, TOCSY, COSY, and HMBC) and Mass spectrometry as under- ... The geometry of compound Egarose was optimized by B3LYP method and 6-31 G (d,p) basis set. [ABSTRACT FROM AUTHOR]

Optimum nutrition is necessary for any infant fed with mother's milk, which facilitates in the development of the infant's growth, bones, brain, immune system and other parameters. All these factors are in turn facilitated largely by the oligosaccharides present in the milk. These oligosaccharides are made up of various monosaccharides as their building blocks comprising of different combinations of sugars. A number of animals have been investigated for their milk oligosaccharide contents; they have shown different biological activities like immuno-stimulants, liver stimulating, pre biotic, anti-viral and many more. In search for some more novel oligosaccharides, milk of Bactarian camel was studied for its oligosaccharide contents. Keeping in mind the biological activities of camel milk as anti-hepatitis, liver stimulant, anti-hypertensive, anti-asthmatic and anti-diabetic, the Bactarian camel's milk was collected in bulk and processed by the modified method of Kobata and Ginsburg incorporating deproteination, microfiltration, gel-filtration and lyophilisation, resulting in isolation of crude milk oligosaccharide mixture. For its further studies, it was acetylated by acetic anhydride in pyridine affording the acetylated oligosaccharide mixture. This was purified by silica gel column chromatography which gave a novel tetrasaccharide Bacuose. Its structure was elucidated by chemical degradation, chemical transformation and physico-chemical techniques such as 1H, 13C and 2D (COSY, TOCSY, HSQC and HMBC) NMR experiments and Mass Spectrometry. The stereoscopic structure of the novel tetrasaccharide Bacuose was determined as under .... [ABSTRACT FROM AUTHOR]

Milk is an excellent source of balanced nutrients and is also responsible for growth of children and nourishment of adults. The oligosaccharides present in milk have numerous biological activities such as antitumor, anticancer, antiviral, antiinflammatory, anticoagulant, antioxidant and immunostimulant activities. These biological activities of milk oligosaccharides depend upon the monosaccharide constituents, their sequence and appended groups. Camel milk contains higher concentration of sialyl oligosaccharides which have shown anti-adhesive effects against certain pathogens as well as important nutrients for brain development. Keeping in mind the biological activities of camel milk and oligosaccharide present therein, it was collected in bulk and was processed by modified method of Kobata and Ginsberg for obtaining its oligosaccharide constituents. During the process camel milk was deproteinated, centrifugated and filtered by microfilter and lyophilized followed by gel filtration HPLC, column chromatography and thin layer chromatography, which resulted in the isolation of a novel milk oligoglycoside namely Camiloside. The stereoscopic structures of this purified compound were elucidated with the help of chemical degradation, chemical transformation and spectroscopic techniques like NMR (1H, 13C, COSY, TOCSY, HSQC and HMBC) and mass spectrometry. The isolated novel camiloside contains a methyl group at its reducing end. It is the first report of any milk oligosaccharide as its methyl glycoside. [ABSTRACT FROM AUTHOR]

Oligosaccharides are an important class of biologically active natural products found in various natural sources including the mammalian milk, these oligosaccharides act as a potent drug against fatal diseases like AIDS, and cancer and used as an immunostimulant. Several oligosaccharides have been isolated from different mammalian milk and were examined in many models for the treatment of human diseases. Large number of bioactive oligosaccharides have been reported and isolated from cow, sheep, goat, buffalo, camel, mare, yak, elephant, and human milk. The medicinal properties of sheep's milk are well defined in Vedic literature. Unani and Ayurvedic medicinal system has also elaborated many biological activities of sheep milk. The sheep milk oligosaccharides have shown anti-inflammatory properties and have also given promising results against tuberculosis in tribal medicinal systems. It was also used for increase of blood platelets reduced after dengue fever. Keeping in mind, the bio efficacy of sheep's milk and the role of oligosaccharides present there in, it was analyzed for its oligosaccharide contents. After processing it by Modified method of Kobata and Ginsberg and its isolation by chromatographic techniques, a novel pentasaccharide, Ariesose, C36H61O26N3, was isolated from sheep's milk. The structure of this novel oligosaccharide was elucidated by chemical transformation, chemical degradation, 1H, 13C, 2D-NMR (COSY, TOCSY, HSQC, HMBC) and mass spectroscopy. [ABSTRACT FROM AUTHOR]

Milk is a primary dynamic biological fluid that is golden standard for nutrition of newborn infants. Besides the other regular constituents it has oligosaccharides in it which are indigestible by the infant yet are consumed by the microbial populations in the developing intestine. These oligosaccharides are believed to facilitate enrichment of a healthy infant gastrointestinal micro biota, often associated with bifidobacteria. Goat milk is a rich source of oligosaccharides that have enormous biological activities such as anti-bacterial, immunological, anti-inflammatory, hypoallergenic and therapeutic properties. It is used against tuberculosis in folk medicine and also helps in the enhancement of platelet count during dengue fever. Goat milk oligosaccharides have antiinflammatory properties and are involved in the repairing process after a dextran sodium sulphate-induced colitis. Keeping in mind the biological importance of goat milk and the role of oligosaccharides, in the present studies, goat milk was analyzed for its oligosaccharide content which led to the isolation of a novel tetrasaccharide, prisose, C28H48O21N2. The structure of the isolated oligosaccharide was elucidated by chemical transformation, chemical degradation, ¹H, 13C, 2D-NMR (COSY, TOCSY, HMBC and HSQC) and mass spectrometry as under. The geometry of compound prisose was optimized by B3LYP method and 6-31 G (d,p) basis set. [ABSTRACT FROM AUTHOR]

Milk Oligosaccharides are an important class of bioactive natural products with immunostimulant activities and are emerging as potent drugs against fatal diseases like cancer and AIDS. Recently a number of natural oligosaccharides have been isolated from milk of various animal origin and were examined in animal models of different human diseases. A number of biologically active oligosaccharides have been isolated from cow, camel, buffalo, human, sheep, mare, yak, elephant and goat milk. The medicinal property of goat milk is well documented in our ancient literature, according to Ayurveda and Unani medicinal systems, enormous biological activities such as anti-bacterial, immunological, anti-inflammatory, hypoallergenic and therapeutic properties have been reported. It is used against tuberculosis in folk medicine and also helps in the enhancement of platelet count during dengue fever. Goat milk oligosaccharides have anti-inflammatory properties and are involved in the repairing process after a dextran sodium sulphate-induced colitis. Keeping in mind the biological importance of goat milk and the role of oligosaccharides, in the present studies, goat milk was analyzed for its oligosaccharide content which led to the isolation of a novel tetrasaccharides, rasose, C26H45O21N. The structure of the isolated oligosaccharide was elucidated by chemical transformation, chemical degradation, ¹H, 13C, 2D-NMR (COSY, TOCSY, HMBC and HSQC) and mass spectrometry as under. The geometry of compound rasose was optimized by B3LYP method and 6-31 G (d,p) basis set. [ABSTRACT FROM AUTHOR]

Milk is a key component for infant nutrition which contain protein, fat and oligosaccharides. Amongst all mammalian's milk, black cow's (Shyamadhenu) milk is well defined for its medicinal properties in the ancient literature which says that Shyamadhenu's milk is used as immuno-stimulant, nourishes the body tissues, acts as natural aphrodisiac, does rejuvenation and improves intelligence. It is also used in heart diseases, leukoderma, increases breast milk in feeding mother, assists in easy movement of intestine and bleeding disorders. Keeping in mind the medicinal importance of Shyamadhenu's milk and simultaneous presence of oligosaccharides into it, we have continued our work for the isolation of some more novel milk oligosaccharides from this milk. For this purpose Shyamadhenu's milk was collected in bulk and was processed by modified method of Kobata and Ginsburg, followed by gel filtration, HPLC and Column Chromatography technique which led to the isolation of a novel milk tetrasaccharide namely asose. Structure of the isolated oligosaccharide was assigned by chemical transformation, chemical degradation, NMR (¹H NMR, 13C NMR), 2D-NMR (COSY, TOCSY, HSQC and HMBC) techniques, and mass spectrometry. The structure of novel isolated oligosaccharide was deduced as under-... [ABSTRACT FROM AUTHOR]

Plant families like Asclepiadaceae have been found to be rich sources of pregnane and cardiac glycosides. Brevoside, a novel pregnane monoglycoside, was isolated from the chloroform extract of the whole plant Sarcostemma brevistigma (family: Asclepiadaceae). The structure of the isolated compound, brevoside, was elucidated by chemical degradation and physicochemical techniques like 1H, 13C, 2D NMR spectroscopy, and ES-MS techniques. The structure of the compound was deduced as 11α-O-4-methoxy benzoyl-20-oxo-pregn-5-ene-3β, 14β - diol -12-O-α-D-cymaropyranoside. [ABSTRACT FROM AUTHOR]

The properties of milk have been of scientific interest from various points of view like evolutionary, nutritionally and medicinally. It is sole nutrient source for newborn infants which is due to their structural diversity. The intestinal micro-biota protects against pathogens during early growth and development. The oligosaccharides isolated from various source of milk play a cardinal role in numerous physiological, pathological and biological activities. This study was aimed to find out the biologically active novel yak milk oligosaccharides. For this purpose 10 L of Yak milk was processed by modified method of Kobata and Ginsberg involving de-proteination, centrifugation and lyophilization followed by gel filtration HPLC and Column Chromatography which resulted into the isolation of a novel yak milk oligosaccharide namely nienose. The structure of Nienose was elucidated by chemical transformation, chemical degradation, ¹H, 13C, 2D-NMR (COSY, TOCSY, HMBC and HSQC) and mass spectrometry. [ABSTRACT FROM AUTHOR]

Oligosaccharides which have been isolated from different bovine milk exhibit high potent biological activities like antiviral, anticancer, antitumor, antioxidant, antibacterial, antifungal, antimicrobial, antihepatitis, anti-inflammatory, anticoagulant, immunostimulant, antituberculosis. Oligosaccharides of cow milk have shown structural resemblance with human milk oligosaccharides; therefore cow milk is currently being used in a variety of health-promoting supplements worldwide. Several scriptures and studies supported the constructive effects of supplementation of cow milk in diarrhea in human with immunedeficiency syndrome, NSAID-induced gastrointestinal disturbances. With a view to isolate biologically active oligosaccharide from Lal-Muha cow (a rare species of cow found in north eastern part of India at high altitude) milk was taken and processed by the modified method of Kobata and Ginsburg followed by gel filtration, HPLC and column chromatography which resulted in the isolation of novel oligosaccharide namely uruose. The structure of isolated oligosaccharide, uruose was elucidated by chemical transformations, chemical degradation, NMR (¹H, 13C 2D COSY, TOCSY, HSQC and HMBC) and mass spectrometry. [ABSTRACT FROM AUTHOR]

Oligosaccharides are the most important carbohydrate constituents of all bacteria, fungi, plants and placental mammals' milk. A number of oligosaccharides have been isolated from various mammalian milk i.e. bear, elephant, donkey, rat, dog, cow, sheep, goat, and camel, which have shown anti-complementary, anti-coagulant, immune-stimulant, viral replications, parasitic infection, cell growth, cell wall adhesion and inflammation activities. It has been seen that the milk oligosaccharides are comprised of various core-units and every core-unit has lactose at its reducing end, besides that the milk oligosaccharides contain glucose, galactose, GlcNAc, GalNAc, fucose and sialic acid at its non-reducing end. The presence of these mono-saccharides and the position of the glycosidic linkages play a definite role in their biological activity. To isolate more novel oligosaccharides, camel milk was chosen for novel milk oligosaccharides which have importance in traditional medicinal systems. Camel milk is used as a remedy for some diseases like tuberculosis juvenile diabetes, liver cirrhosis, rickets, constipation, asthma, and certain viral infections. For this purpose Camel milk was collected in bulk and processed by the modified method of Kobata and Ginsburg followed by gel filtration, HPLC and column chromatography which resulted in the isolation of a novel oligosaccharide namely mesose. The structure of the isolated oligosaccharide was elucidated by chemical transformations, chemical degradation, NMR (¹H, 13C and 2D COSY, TOCSY, HSQC and HMBC) and mass spectrometry. [ABSTRACT FROM AUTHOR]

Milk is one of the most important source of biologically active oligosaccharides. Many oligosaccharides has been isolated from various milk which have exhibited potent biological activities such as anti-tumor, anti-viral, anti cancer, anti-inflammatory, anti-coagulant, immunostimulant and hypoglycemic activities and they have also been used as certain biomarkers. These biological activities of milk oligosaccharides were based on different constituent monosaccharides and linkages which normally contain six monosaccharides namely, glucose, galactose, N-acetyl-glucosamine, N-acetyl-galactosamine, fucose, and N-acetylneuraminic acid. These monosaccharides combine in different order to form a large number of oligosaccharides and show different biological activities. Presence as galactose and sialic acid are in milk oligosaccharides were reported to develop the brain of infants. Milk oligosaccharides have a unique structure to act as a soluble ligand against infective bacteria to protect the gastrointestinal, respiratory, and urinary tracts. It is recently discovered that a trace amount of milk oligosaccharides are absorbed through the gut and interact directly with the immune system to modulate the immune response. We have chosen Lal-Muha cow (a rare species of cow found in north eastern part of India at high altitude) milk in search of novel milk oligosaccharides which have importance in folk medicine. A number of studies supported the constructive effects of supplementation of cow milk in diarrhea in human with immune-deficiency syndrome, NSAID-induced gastrointestinal disturbances. For this Lal-Muha cow's milk was collected in bulk and processed by the modified method of Kobata and Ginsburg followed by gel filtration, HPLC and column chromatography which resulted in the isolation of novel oligosaccharide namely Taurose. The structure of isolated oligosaccharides was elucidated by chemical transformations, chemical degradation, NMR (¹H, 13C and 2D COSY, TOCSY, HSQC and HMBC) and mass spectrometry. [ABSTRACT FROM AUTHOR]

Milk provides number of novel oligosaccharides depending on the nature of their origin and to which mammals the milk belongs and has shown varied biological activities such as anti-tumor, anticancer, anticomplementary, hypoglycemic, anti-inflammatory anticoagulant, antiviral, immunostimulant and immunological activities. Milk oligosaccharides have the potential to produce immuno-modulation effects, significant influence on intestinal mineral absorption and in the formation of the brain and central nervous system. The prebiotic properties of oligosaccharide highly depend on structural conformation, including their degree of polymerization, monosaccharide composition, and their glycosidic linkages. Determination of structures of novel oligosaccharide is challenging because of a range of molecular diversity and complexity of molecular structure. Due to compositional resemblance of cow's milk with human milk and the medicinal importance of cow's milk given in Indian medicinal system i.e. Ayurveda, a rare species of cow found in hills of Sikkim (India) commonly known as Lal-Muha at 5,410 ft was considered a potential source of biological active oligosaccharides. For this purpose Lal-Muha cow milk was collected in bulk and processed by the modified method of Kobata and Ginsburg followed by gel filtration, HPLC and column chromatography which resulted in the isolation of novel oligosaccharide namely, Usose. The structure of isolated oligosaccharides was elucidated by chemical transformations, chemical degradation, NMR of neutral and acetylated oligosaccharide (1H, 13C and 2D COSY, TOCSY, HSQC and HMBC) and mass spectrometry. ... [ABSTRACT FROM AUTHOR]

Oligosaccharides are the most important carbohydrate which is natural constituents of all bacteria, fungi, plants and placental mammal's milk. The milk is a rich source of oligosaccharides which normally contain six monosaccharides namely, glucose, galactose, N-acetyl-glucosamine, N-acetyl-galactosamine, fucose, and Nacetyl- neuraminic acid. These monosaccharides combine in different order to form a large number of oligosaccharides. Milk provides number of novel oligosaccharides depending on the nature of their origin and to which mammals the milk belongs and has shown varied biological activities such as anti-tumor, anticancer, anticomplementary, hypoglycemic, anti-inflammatory, and anticoagulant, antiviral, immunostimulant and immunological activities. Several studies supported the constructive effects of supplementation of cow milk in diarrhea in human with immune-deficiency syndrome, NSAID-induced gastrointestinal disturbances. To isolate the oligosaccharide from Lal- Muha cow (a rare species of Cow found in north eastern part of India at high altitude) milk was chosen in search of novel milk oligosaccharides which have importance in medicinal field. For this purpose Lal- Muha cow milk was collected in bulk and processed by the modified method of Kobata and Ginsburg followed by gel filtration, HPLC and column chromatography which resulted in the isolation of novel oligosaccharide namely Rusose. The structure of isolated oligosaccharides was elucidated by chemical transformations, chemical degradation, NMR (1H, 13C and 2D COSY, TOCSY, HSQC and HMBC) and mass spectrometry. ... [ABSTRACT FROM AUTHOR]

Plants of Asclepiadaceae and Apocynaceae families are rich sources of pregnane and cardiac glycosides, which are known to possess anti-inflammatory, anti-cancer, immunostimulant, cardiotonic and hypoglycemic activities. Ichnocarpus frutescens, a species of the Apocyanaceae family, has a large number of uses in the traditional medicine, including treatment for fever, bronchitis, rheumatism, asthma, cholera, and leucoderma. In search for more biologically active compounds, a novel compound, carpuside, was isolated from the chloroform extract of aerial part of the plant I. frutescens. The structure of the isolated glycoside, carpuside, was confirmed by the chemical transformation / degradation and physicochemical techniques like ¹H, 13C, 2D NMR, and FABMS techniques. The structure of the novel compound, carpuside, was deduced as calogenin-3-O-α-L-fucopyranosyl- (1->4)-α-L-digitoxopyranoside. [ABSTRACT FROM AUTHOR]